Disazo dyestuffs insoluble in water



United States Patent in which A represents a benzene residue, Brepresents a benzene or naphthalene residue and W represents the groupof the formula:

in which one Z represents a hydrogen atom or a CH group and the othersrepresent hydrogen atoms, R and R each represent hydrogen atoms, alkylgroups of low molecular Weight (perferably having less than 5 car-honatoms), hydroxy'alkyl groups of low molecular weight, acetyl orcyclohexyl or R and R may form part of a saturated heterocyclic groupsuch as a morphohno or piperidino ring.

The dyestufis of Formula I may be prepared by coupling amides of FormulaII derived from salicycllc or cresotic acids with diazo derivatives ofthe monoazo dyestuffs of the formula:

U Y I 1 E i (III) in which U and X represent hydrogen or chlorine atomsor -CH3, C2H5, ()CH3, OC2H5, or --OCH CH OH groups, V and Y representhydrogen atoms or -CH C H OCH -OC H or -OCH CH OH groups, X and Vhowever being able to form part of a naphthalene ring system instead of3,331,829 Patented July 18, 196'? lCe corresponding with the abovedefinitions, and the benzene ring A may be substituted by CH C H OCH -OCH OCH CH OH, -NHCOCH or NO groups or chlorine atoms.

The amino-monoazo dyestufis corresponding to the Formula III may beobtained by coupling the diazo derivative of a benzene amine ANH with anamine BNH capable of coupling in the para position, of the aniline oralpha-naphthylamine series and their substituted derivatives.

The disazo compounds of Formula I are excellent dyestuffs. Sparinglysoluble in Water, they are taken up from aqueous dispersions on tohydrophobic fibres, such as synthetic polyamide fibres like Nylon andRilsan fibres based on cellulose esters, for example the acetate,diaeetate or triacetate of cellulose, and fibres based on polyesters,notably ethylene glycol polyterephthalate.

Shades ranging from orange to brown are obtained, which have excellentfastness to light, sublimation, washing and perspiration.

The great interest of the invention lies in the fact that homogeneousbrowns are thus obtained. Up to the present most brown shades have beenobtained by mixing several elements. If the components have not exactlythe same curves for going on to the fibre and the same saturation valueswith regard to the fibres, a different shade results according to theiruse. The invention enables this disadvantage to be. avoided.

The following examples illustrate the present invention without limitingit. The parts indicated are by weight unless the'contrary is stated.

Example 1 19.7 parts of 4-amino-azobenzene are mixed with 40 parts byvolume of 19 B. hydrochloric acid, made up to a volume of 700 parts anddiazotised at C. by the addition of 13.8 parts by volume of a 50%solution of sodium nitrite. The solution of the diazo derivative isslowly introduced into a solution of 15.2 parts of the amide ofp-cresotic acid in 500 parts by volume of an alkaline solution preparedby means of 6.5 parts by volume of 35 B. caustic soda and 30 parts ofsodium carbonate. The coupling medium is filtered, and the dyestuifcollected is mixed with dispersing agents such as dinaphthylmethanesulphonates, dried and ground. On dyeing fibres based on polyesterseither by means of vehicles at a temperature below C. or withoutvehicles at a temperature above C., a yellow-brown shade is obtainedwhich has excellent fastness to wet tests, light and sublimation.

Example 2 9.3 parts of aniline are diazotised in the usual way. Thediazotisation bath is introduced into an acid solution of 12.3 parts ofm-anisidine while reducing the acidity of the mixture by the addition ofsodium acetate. When coupling is finished, the reaction mixture isfiltered. The monoazo compound obtained is then rediazotised like the4-amino-azobenzene in Example 1 and coupled with 15.2 parts of the amideof o-cresotic acid in alkaline medium. The coupling medium is filtered;the dyestuff obtained is mixed with dispersing agents such asdinaphthylmethane sulphonates, dried and ground. When applied onpolyester fibres according to the usual dyeing methods, with or withouta vehicle, it gives a full-bodied brown orange possessing excellentfastness to wet tests, sublimation and light.

The following table gives examples of dyestuffs con- A strip ofpolyester fabric is foularded several times in forming to Formula I.this d'ISPeISIOII and heat-fixed for 1 minute at 200 C.

Substituents of B Substituents of W Example No. Substituents of A X V YU Z1 Z2 Z3 R1 R1 CH H H CH; H H H H CHgCH OH H H CH H H H H H C4 9 OCH HH H H H H C H C7H5 OCH H H H H H H NHCOCH OCH H OOH; H H H H H H CH H HH H H H Cyclohexyl H 01 H H H H H H Morpholino NHCOCH H H H H H H H H HH H OH; H H H CH H CH H H OCH; H H H CH3 H H 4-hydroxyethoxy OCH; H H HOH; H H 4-methoxy OCH; H OCH H CH H H 16-- 4-nitro H H H CH H H H H H CHH H H H H CH H H H H H H H CH3 H CgHs H H H CH H H H H H CH H H H H HCH3 H OCHa H H H CH H OCHa H H H CH3 a HC CH H H H H CH H H CHCH 26 HCCH OCH; H H H CH H H CHCH 27 4-methoxy OCH H H H H CH3 H H 28-- H H H HH CH3 H CzH5 29 2-methyl H CH3 H H CH H C3115 OCH H H H H CH H CzHs HOCHs OCHa H H CH3 H H OCHzCHzOH H H H H CH3 H CH3 yellow-brown shades,those of Examples 6, 7 and 15 give 4 orange-brown shades, those ofExamples 3 to 5 inclusive and 8, 10 and 18 give brownish orange shades,the dyestufi" of Example 11 gives an orange-yellow shade, those 7 Thispaste is applied on a grooved roller on a fabric of polyester fibrespreviously desized in the hot by alkaline Washing. The colour is fixedby steaming under pressure at 130140 C. The fabric is rinsed and treatedin the hot with an alkaline reducing bath containing 1 to 2 g. per litreof an octylphenol/ethylene oxide condensate.

Since the dyestufi is very fast to sublimation, it remains on the fibreand does not migrate on to the cold parts of the apparatus.

We claim:

Disazo dyestufis of the formula:

of Examples 12 to 14 inclusive and 17 give yellow orange shades, that ofExample 9 give an orange shade and that of Example 16 gives abrown-orange shade.

Example 33 )C i A printing paste is prepared which is composed of thefollowmg elamems: Parts wherein the benzene nucleus A may be substitutedby least one member selected from the rou consistin D estufi of Exam le19 6 at g P g soydium methylens dinaphthylsulphonate 14 of chlorine andthe methyl, ethyl, methoxy, ethoxy, hy- Monoeth 1 ether of ethylene g} yc 01 5O droxyethoxy, acetylamino and nrtro groups, U and X each Water y300 represent a member selected from the group consisting Aqueoussolution of sodium chlorate containing 300 of hydrogen and .chlonne andthe methyl ethyl methoxy 0 er litre 30 ethoxy, acetylamino andhydroxyethoxy groups, V and Y g traoacamh 600 each represent a memberselected from the group con- 5 sisting of hydrogen and the methyl,ethyl, methoxy,

ethoxy and hydroxyethoxy group, X and V taken together represent the CHCH-CH CH radical and W represents the residue of a coupling compound ofthe formula:

The fabric is coloured a yellow brown shade having exi cellent fastness,the reserved parts being perfectly white. Z1 0 Example 34 z a Afoularding bath composed of the following elements J is prepared: A3

Parts Dyestutf of Example 33 30 Sodium methylene dinaphthylsulphonate 7in which one Z represents a member selected from the Starch tragacanth 5group consisting of hydrogen and the methyl group, and

Quantity of water sufiicicnt for 100 the other two represent hydrogenatoms, R and R repre- 5 6 sent a member selected from the groupconsisting of References Cited hydrogen, alkyl groups having up to fourcarbon atoms, UNITED STATES PATENTS hydroxy-a1kyl groups having up tofour carbon atoms and the acetyl group, R represents a cyclohexyl groupif 3,071,571 1/1963 Gross et a1 260 187 R represents a hydrogen atom, Rand R together with 5 the nitrogen atom form a heterocyclic ringselected from CHARLES PARKER Primary Exammer' the group consisting ofmorpholine and piperidine rings. D. M. PAPUGA, Examiner.

